Aggregation and Adsorption Properties of Tetramethylsulfonatoresorcinarenes and their Associates with Nonionogenic Guest Molecules in Aqueous Solutions

Morozova, Julia E.; Kazakova, E. Kh.; Gubanov, Eduard P.; Макарова, Н. А.; Archipov, V. P.; Timoshina, T. V.; Idijatullin, Zaymil Sh.; Habicher, Wolf D.; Коновалов, А. И.

doi:10.1007/s10847-005-9034-5

Cited by 13 publications

(11 citation statements)

References 16 publications

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“…Macrocycle 1 with four methyl substituents in the lower rim is not prone to aggregation in all of the applied solvents. Its D s remains unchanged in the con centration range of 0.1-50 mM [20][21], while the values of R H calculated from D s in water, DMSO, and methanol are close to R Hm calculated using the HYDRONMR software package [32].…”

Section: Experimental Datasupporting

confidence: 52%

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Aggregation and complexation in a series of tetramethylenesulfonate-substituted calix[4]resorcinarenes

et al. 2012

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NMR methods are employed to study the effects of inorganic salts, solvents, and guest molecules of methylviologen (MV 2+ ) and choline (Ch + ) on the aggregation properties of water soluble tetramethylene sulfonate substituted calix[4]resorcinarenes containing methyl (1), amyl (2), and heptyl (3) substituents in the lower rim. It is established that, in aqueous solutions at concentrations of 1-10 mM, compound 1 exists in the monomeric form; the size of aggregates of amphiphilic compound 2 gradually increases (aggregation number varies from 1 to 20); and hydrophobic compound 3 dissolves only in slightly alkaline aqueous solu tions to form large micellar aggregates. For macrocycles 2 and 3, which are inclined to aggregation, the aggre gate sizes depend on the concentration, pH, and ionic strength of solutions, as well as on the presence of organic solvents. Macrocycle 1 binds guest molecules Ch + and MV 2+ to yield inclusion complexes. In the presence of aggregates of substance 2, the binding of guest molecules is more efficient and they are encapsu lated between the rim of one molecule and the tail of another molecule of compound 2. The presence of guest molecules enhances the aggregation of macrocycle 2. In the case of compound 3 solutions, guest Ch + mole cules are predominantly localized in the hydrophobic environment of alkyl substituents of the host.

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Section: Experimental Datasupporting

confidence: 52%

“…1) with different degrees of hydrophobicity that enabled us to determine their states in the processes of both aggregation and com plexation with charged and neutral guest molecules [19][20][21][22][23]. It was shown that, in 1-10 mM solutions, macrocycle 2 forms aggregates [23].…”

Section: Introductionmentioning

confidence: 99%

Aggregation and complexation in a series of tetramethylenesulfonate-substituted calix[4]resorcinarenes

et al. 2012

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“…The group later reported a comparative study into the interactions of sulfonated calix[4]resorcinarenes bearing alkyl chains of either 1 carbon (methyl group) or 5 carbons (pentyl) on the lower rim with small molecules capable of multiple non-covalent interactions in aqueous media [23]. This study presented evidence that sulfonated calix [4]resorcinarenes are able to aggregate with the hydrophobic pentyl moieties entering the hydrophobic inner core of neighbouring calyxes even in the presence of small molecular guests.…”

Section: Introductionmentioning

confidence: 99%

Investigation into Drug Solubilisation Potential of Sulfonated Calix[4]Resorcinarenes

Hoskins¹,

Papachristou²

2016

J Nanomed Nanotechnol

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“…For calix[n]arene and calix[n]resorcinarene films deposited at the water -air interface orientation of the upper rim of the cavity towards aqueous phase favours cation -p interactions. They can be detected tensiometrically (5), but usually they are not strong enough to affect the morphology of the film. On the other hand, molecules of the interfacial film can participate in at least two other kinds of interactions.…”

mentioning

confidence: 99%

“…The common trait shared by these compounds is their amphiphilic nature (5). While in solution, depending on the concentration, two patterns of their complexation behaviour towards large polymeric molecules can be distinguished.…”

mentioning

confidence: 99%

Monolayers and Langmuir–Blodgett films of amphiphilic tetramethylsulphonatocalix[4]resorcinarene and their interactions with polyethyleneimine and caeruloplasmin

Мельникова

Kazakova

Guljaev

et al. 2009

Supramolecular Chemistry

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2009) Monolayers and Langmuir-Blodgett films of amphiphilic tetramethylsulphonatocalix[4]resorcinarene and their interactions with polyethyleneimine and caeruloplasmin, Supramolecular Chemistry, 21:6, 532-538,The paper deals with the surface films of amphiphilic tetramethylsulphonatocalixresorcinarene (R ¼ C 11 H 23 ) 1 insoluble in water but forms rigid stable non-collapsing films at the water -air interface. Compression isotherms were used to investigate the interactions of the macrocycle films with two polymers fed to the aqueous subphases: synthetic -polyethyleneimine (PEI) and natural -an oxidase enzyme caeruloplasmin (CP). The interactions of the surface films of 1 with these substrates are predominantly dictated by the nature of the macromolecules and not by macrocycle interactions with their individual fragments. CP having retained its globular structure was extracted in the layer of 1 and became the dominating component of the film. The synthetic macromolecule of PEI, six times lower in its weight than CP, did not affect the morphology of the interfacial film, involved in the interactions only with its hydrophilic part directed inside the water.

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Aggregation and Adsorption Properties of Tetramethylsulfonatoresorcinarenes and their Associates with Nonionogenic Guest Molecules in Aqueous Solutions

Cited by 13 publications

References 16 publications

Aggregation and complexation in a series of tetramethylenesulfonate-substituted calix[4]resorcinarenes

Aggregation and complexation in a series of tetramethylenesulfonate-substituted calix[4]resorcinarenes

Investigation into Drug Solubilisation Potential of Sulfonated Calix[4]Resorcinarenes

Monolayers and Langmuir–Blodgett films of amphiphilic tetramethylsulphonatocalix[4]resorcinarene and their interactions with polyethyleneimine and caeruloplasmin

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